Synthesis Of Tripod BODIPY Compounds Bearing N-hydroxysuccinimide Ester

Fluorescence spectroscopy and fluorescence imaging are becoming indispensable tools in today's scientific research.Fluorescence analysis had the advantages of high selectivity,high sensitivity and high fluorescence quantum yield.Organic fluorescent dyes had been widely used in protein labeling,DNA detection and environmental testing.N-hydroxysuccinimide had a pivotal application in the tumor diagnosis,immunoassay,affinity chromatography,antigen isolation and other fields.In this paper,we obtained the BODIPY fluorescent dyes with NHS ester.In order to verify its reactivity,through the reaction between BODIPY fluorescent dye with NHS ester and glycine methyl ester,we successfully obtained the amino acid methyl ester with BODIPY fluorophore.A total of 7 new BODIPY fluorescent dyes were synthesized,which were characterized by NMR,MS and FT-IR spectra.There were following exploration and conclusions:1.When benzyl p-hydroxybenzoate was introduced into the cyanuric chloride,the activity of the product was lower than that of other fluorescent compounds because of its electronic effects.2.For the hydrogenolysis of tripod BODIPY benzyl esters in palladium-carbon and hydrogen atmosphere,attention should be paid to the stability of the compound.The reaction time was generally not more than 3 h at room temperature.Solvent had little effect on the reaction.3.NHS active esters were prepared by N,N'-disuccinimidyl carbonate(DSC)method,When P-chlorophenol was attached,a DAMP-catalyzed nucleophilic substitution happened on the1,3,5-triazine ring,resulting in the breakage between the BODIPY fluorophore and triazine ring.The target NHS ester was successfully received when the non-nucleophilic was used.4.The photophysical properties were analyzed.The maximum absorption wavelength was around 502 nm.Fluorescence quantum yield was 37.41%-63.41%.